Oxy Containing Reactant Patents (Class 568/361)
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Patent number: 6201155Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.Type: GrantFiled: August 3, 1999Date of Patent: March 13, 2001Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, August Rüttimann
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Patent number: 6191312Abstract: A process for preparing a bicyclooctanone, in particular 1,5-dialkylbicyclo[3.2.1]octan-8-one, by reacting a bicyclooctanol, in particular dialkylbicyclo[3.2.1]octan-8-ol, with a. a catalyst applied to an active-carbon support and comprising heteropolyoxometallate anions of vanadium, molybdenum and phosphorus, and also a corresponding alkali-metal, alkaline-earth-metal and/or ammonium counter ion, and b. a gaseous, oxygen-containing oxidizing agent.Type: GrantFiled: August 3, 1999Date of Patent: February 20, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Alfred Hagemeyer, Rolf Peter Schulz, Harald Werner, Uwe Dingerdissen, Klaus Kühlein, Heinz Alexander
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Patent number: 6184420Abstract: Unsaturated ketones of the formulae Ia and Ib are prepared by a process consisting of the combination of the following reactions: a) The conventional reaction of an allyl alcohol of the formula IIa or a propargyl alcohol of the formula IIb with an isopropenyl ether of the formula III with formation of a ketal of the formula IV as a byproduct, b) preparation of the isopropenyl ether of the formula III by reacting a ketal of the formula IV with propyne or allene, or a mixture thereof in the gas phase at elevated temperatures in the presence of a heterogeneous catalyst containing zinc or cadmium together with silicon or oxygen, and c) feeding the ketal of the formula IV formed in the reaction (a) into stage (b) for the preparation of the isopropenyl ether of the formula III again.Type: GrantFiled: September 10, 1998Date of Patent: February 6, 2001Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Stefan Kaeshammer, Heinz Etzrodt, Wulf Kaiser
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Patent number: 6166091Abstract: 2,3,4-trihydroxycyclopentanone represented by the following formula [I], its optically active substance or salt thereof.Type: GrantFiled: September 29, 1999Date of Patent: December 26, 2000Assignee: Takara Shuzo Co., Ltd.Inventors: Kaoru Kojima, Katsushige Ikai, Tatsuji Enoki, Nobuto Koyama, Ikunoshin Kato
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Patent number: 6166257Abstract: The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative.The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative.Type: GrantFiled: March 24, 1999Date of Patent: December 26, 2000Assignee: Rhodia ChimieInventors: Francois Mathey, Frederic Robin, Francois Mercier, Michel Spagnol
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Patent number: 6162758Abstract: In the dehydrogenation of secondary alcohols in the presence of a catalyst comprising zinc oxide and calcium carbonate at elevated temperature in the gas phase, secondary cyclic alcohols are used and the dehydrogenation is carried out in the presence of hydrogen and a catalyst whose active components comprise from 30 to 60% by weight of zinc oxide and from 40 to 70% by weight of calcium carbonate in the calcite modification.Type: GrantFiled: September 3, 1998Date of Patent: December 19, 2000Assignee: BASF AktiengesellschaftInventors: Franz Josef Brocker, Michael Hesse, Robert Markl
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Patent number: 6111125Abstract: A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.Type: GrantFiled: March 3, 1995Date of Patent: August 29, 2000Assignee: BASF AktiengesellschaftInventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
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Patent number: 6111144Abstract: A process for the preparation of a compound having the formula: ##STR1## in which a compound having the formula: ##STR2## is treated with a base and a silylating agent.Type: GrantFiled: August 20, 1998Date of Patent: August 29, 2000Assignee: Florida State UniversityInventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
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Patent number: 6031139Abstract: The use of polar organic solvent as the solvent in the direct fluorination, to make an .alpha.-fluoroketone, of an enol ester or enol trialkylsilyl ether of a compound containing a tautomerisable ketone group, the solvent being relatively inert to fluorine and one in which the enol ester or enol trialkylsilyl ether is relatively stable to hydrolysis. Preferably the solvent is anhydrous, e.g. anhydrous acetonitrile. Alternatively commercial formic acid containing 3% water may be used with a said enol ester.Type: GrantFiled: February 5, 1998Date of Patent: February 29, 2000Assignee: F2 Chemicals LimitedInventors: John Hutchinson, Richard Dickinson Chambers
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Patent number: 6011182Abstract: The present invention relates to a process for preparing 2-cyclo-alkenones of the formula I ##STR1## which comprises subjecting a 2-alkoxycycloalkanone and/or a 2-hydroxyalkanone ketal, in which n is an integer from 0 to 20, m is 0, 1, 2 or 3 and R is alkyl, alkylaryl, aryl, arylalkyl, alkenyl or alkynyl, to an elimination reaction in the gas phase on an acidic heterogeneous catalyst.Type: GrantFiled: February 1, 1999Date of Patent: January 4, 2000Assignee: BASF AktiengesellschaftInventors: Matthias Eiermann, Klaus Ebel, Jorg Botzem
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Patent number: 6002046Abstract: Cyclopropyl alkyl ketones are separated from 3-acyltetrahydrofuran-2-ones by adding an alcohol, water or a water/alcohol mixture to a reaction product containing C.sub.1-4 -alkyl cyclopropyl ketone and 4,5-dihydro-2-alkylfuran by-product and an acid catalyst and reacting the by-product with the added alcohol, water of water/alcohol mixture before, during or after distilling said reaction product; and effectively separating C.sub.1 -.sub.4 -alkyl cyclopropyl ketone from reaction by-products.In the preparation of cyclopropyl alkyl ketones from 3-acyltetrahydrofuran-2-ones very reactive 4,5-dihydro-2-alkylfurans are also produced. By reacting such compounds with nucleophilic compounds, such as alcohols or water, before, during or after distillation of the reaction products, it is possible reliably to separate off the 4,5-dihydro-2-alkylfurans as high-boiling addition compounds.Type: GrantFiled: March 8, 1999Date of Patent: December 14, 1999Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Wolfgang Kleemiss, Udo Jegelka, Michael Korell
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Patent number: 5998674Abstract: Method of producing a bromine compound having an aliphatic unsaturated bond which includes reacting a compound having an aliphatic unsaturated bond represented by the following general formula (1) with bromine:R.sup.1 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.2 (1)to produce a bromine compound represented by the following formula (2):R.sup.3 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.4 (2)wherein Ar.sup.1, Ar.sup.2 and Y are the same as defined in the above general formula (1) , and R.sup.3 and R.sup.4 are groups obtained by saturating the unsaturated groups of R.sup.1 and R.sup.2 in the above general formula (1) with bromine, respectively.The reaction is carried out in the presence of a solvent which is inactive in the reaction, and a substantial amount of the heat of reaction is removed from a reaction system by the vaporization of the solvent or bromine. A high-purity bromine compound in high yield which is useful as flame retardant, can be obtained.Type: GrantFiled: August 21, 1998Date of Patent: December 7, 1999Assignee: Teijin Chemicals, Ltd.Inventors: Yutaka Taketani, Haruhisa Hoshimi, Masanori Monri, Seiichi Tanabe, Yasuhiro Shimidzu
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Patent number: 5994589Abstract: A process for preparing 2,5,6-trimethyl-2-cyclohexen-1-one by reacting diethyl ketone with crotonaldehyde or a compound which is converted under the chosen reaction conditions into crotonaldehyde, in the presence of basic agents at elevated temperature, which comprisesa) simultaneously pumping one mole of crotonaldehyde or one mole of a compound which is converted under the reaction conditions into crotonaldehyde, about 5 to 30 moles of diethyl ketone and the aqueous solution or suspension of a strong base, through separate lines or at least partly in the form of a suitable mixture, continuously into a pressure vessel, which is heated where appropriate and which ensures vigorous mixing, in such a way thatb) the reaction temperature is between 150.degree. C. and 350.degree. C., and the average residence time in the pressure vessel is only about 0.1 second to 20 minutes.Type: GrantFiled: March 10, 1999Date of Patent: November 30, 1999Assignee: BASF AktiengesellschaftInventors: Detlef Ruff, Wolfram Burst, Wulf Kaiser, Manfred Stroezel
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Patent number: 5892123Abstract: A method is disclosed for catalytically decomposing cyclododecyl hydroperoxide into cyclododecanone and cyclododecanol using a chromium catalyst.Type: GrantFiled: February 3, 1998Date of Patent: April 6, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Howard Wayne Anderson, James Bernard Sieja
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Patent number: 5728890Abstract: A cycloalkylhydroperoxide, preferably having a C.sub.5-20 cycloalkyl group, is decomposed by bringing it into contact with a ruthenium complex of the formula:?RuCl.sub.2 L.sub.n !.sub.m (I)wherein L=a neutral ligand, n=1-4 and m.gtoreq.1, for example, ?RuCl.sub.2 (PPh.sub.3).sub.3 !, to produce a cycloalkanol and cycloalkanone.Type: GrantFiled: January 30, 1996Date of Patent: March 17, 1998Assignee: Ube Industries, Ltd.Inventors: Toshikazu Hamamoto, Mitsuo Yamanaka, Takato Nakamura, Tetsuro Shimano
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Patent number: 5723632Abstract: The present invention provides a method of synthesizing compounds of formula (I): ##STR1## wherein R and R' are independently (C.sub.1 -C.sub.4)alkyl.Type: GrantFiled: August 8, 1996Date of Patent: March 3, 1998Assignees: MGI Pharma, Inc., Regents of the University of CaliforniaInventor: Trevor C. McMorris
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Patent number: 5712416Abstract: Process for preparing benzoquinones by oxidation of phenols in the presence of a diluent and of an oxygen-transferring catalyst which contains a heavy metal ion bound in a complex, wherein oxygen, hydrogen peroxide, a compound which liberates hydrogen peroxide, an organic hydroperoxide, a percarboxylic acid or peroxomonosulfuric acid or salts thereof are used as oxidizing agent, and wherein the oxygen-transferring catalyst is from the class of iron, manganese or chromium tetraaza?14!annulenes.Type: GrantFiled: November 27, 1995Date of Patent: January 27, 1998Assignee: BASF AktiengesellschaftInventor: Thomas Gessner
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Patent number: 5654489Abstract: There is provided a process for producing an alicyclic diketone compound represented by the formula (1) ##STR1## wherein X is a single bond, --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --O-- or --SO.sub.2 --, R.sup.1 and R.sup.2 each represents an alkyl group having 1 to 6 carbon atoms, m and n are 0 to 2, comprising dehydrogenating an alicyclic diol compound represented by the formula (2) ##STR2## wherein X, R.sup.1, R.sup.2, m and n are as defined above in a liquid phase in the presence of at least one member selected from the group consisting of copper type catalysts and Raney type catalysts.Type: GrantFiled: July 21, 1995Date of Patent: August 5, 1997Assignee: New Japan Chemical Co., Ltd.Inventors: Shuji Kawai, Noboru Araki, Hiroshi Itoh
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Patent number: 5625099Abstract: Abstract of the Disclosure: Compounds of the formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals ##STR2## and a process for preparing these compounds by reacting an alkenyne of the formula II ##STR3## in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III ##STR4## and the use of the compounds of the formula I for preparing astaxanthin, are described.Type: GrantFiled: May 23, 1995Date of Patent: April 29, 1997Inventors: Hansgeorg Ernst, Walter Dobler, Joachim Paust, Udo Rheude
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Patent number: 5600014Abstract: There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.Type: GrantFiled: March 24, 1995Date of Patent: February 4, 1997Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Tomas Hudlicky, Martin Mandel
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Patent number: 5446203Abstract: Alternative methods for synthesizing haloenones and haloakenes and their use as starting materials for synthesis of substituted or unsubstituted alkyl and aryl substituted enones and alkenes, including tamoxifen and tamoxifen analogs, using such haloenones and haloalkenes.Type: GrantFiled: July 29, 1993Date of Patent: August 29, 1995Assignee: New York UniversityInventor: Edward McNelis
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Patent number: 5360937Abstract: Bisketals of 1,3-cyclobutanedione with monovalent and divalent alcohols as well as processes for their production from 1,3-cyclobutanedione or from 3-acetoxy-2-cyclobuten-1-one contained in the distillation residues of the diketene production. The bisketals are suitable intermediate products for the production of squaric acid, for the production and/or purification of 1,3-cyclobutanedione, or as a stable form for storage or substitute for this unstable dione.Type: GrantFiled: March 22, 1993Date of Patent: November 1, 1994Assignee: Lonza Ltd.Inventor: Barry Jackson
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Patent number: 5276176Abstract: Described are alpha, 3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition having from about 85 up to about 90% by weight of a compound having the structure: ##STR1## and from about 10 up to about 15% by weight of a compound having the structure: ##STR2## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is hydrogen or acetyl with the proviso that when R.sub.1 is methyl, R.sub.2 is hydrogen; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alpha, 3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition.Type: GrantFiled: January 8, 1993Date of Patent: January 4, 1994Assignee: International Flavors & Fragrances Inc.Inventor: Anthony T. Levorse, Jr.
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Patent number: 5266729Abstract: A process for the preparation of tricyclo[5.2.1.0.sup.2,6 ]decan-8(9)-one by the conversion of 8(9)-hydroxytricyclo[5.2.1.0.sup.2,6 ]dec-3-ene by means of a supported catalyst containing nickel and magnesium oxide at elevated temperature and, if necessary, at elevated pressure.Type: GrantFiled: August 18, 1992Date of Patent: November 30, 1993Assignee: Hoechst AktiengesellschaftInventors: Hanswilhelm Bach, Werner Kohl, Gregor Deckers, Detlef Kampmann, Claus Kniep
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Patent number: 5227530Abstract: Conversion of alcohol to organic compounds which comprises contacting the alcohol with a heterogeneous catalyst composition comprising crystallineCu.sub.2-X Cr.sub.y Al.sub.6-y B.sub.4 O.sub.17 M.sub.m M'.sub.nwhere M is a divalent metal, M' is a monovalent metal, m is a number in a range from 0 to 0.8, n is a number in a range from 0 to 1.6, X is a number in a range from 0 to 10 0.8 and is equal to the sum of m and n/2, and y is a number in a range from 0.01 to 3, having a characteristic X-ray diffraction pattern.Type: GrantFiled: March 24, 1992Date of Patent: July 13, 1993Assignee: Amoco CorporationInventors: Larry C. Satek, Patrick E. McMahon
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Patent number: 5206442Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.Type: GrantFiled: February 14, 1992Date of Patent: April 27, 1993Assignee: BASF AktiengesellschaftInventors: Christiane Mackenroth, Ernst Buschmann
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Patent number: 5200538Abstract: The present invention provides an optically active 2-methylenecyclopentanone derivative represented by the general formula ##STR1## (wherein R.sup.1 is a protective group for hydroxyl, and the symbol * represents as asymmetric carbon atom).Type: GrantFiled: May 27, 1992Date of Patent: April 6, 1993Assignee: Daiso Co., Ltd.Inventors: Takashi Takahashi, Yoshikazu Takehira
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Patent number: 5164365Abstract: The present invention concerns the novel odorant 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, I, a process for the manufacture of I, novel intermediates used in the process and fragrance compositions containing I. ##STR1## The process for the manufacture of 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone comprises hydroborating 1,1,2,3,3,6-hexamethyl-4,7-dihydroindane and oxidizing the hydroboration product to 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, or reductively alkylating, especially methylating, 5-nitro-1,1,2,3,3,6-hexamethylindane and converting the resulting 5-dialkyl-amino-1,1,2,3,3,6-hexamethylindane into 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone by reduction of the benzene ring and hydrolysis of the resulting enamine.Type: GrantFiled: February 26, 1991Date of Patent: November 17, 1992Assignee: Givaudan CorporationInventors: Jean-Pierre Bachmann, Daniel Helmlinger, Mario Pesaro
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Patent number: 5113021Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.Type: GrantFiled: September 6, 1990Date of Patent: May 12, 1992Assignee: Givaudan CorporationInventors: Georg Frater, Daniel Helmlinger
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Patent number: 5103066Abstract: The invention relates to a catalytic dehydrogenation of alcohols to produce ketones and/or aldehydes. The catalyst comprises a dehydrogenation metal and a non-acidic microporous crystalline material as a support. The support may contain indium, tin, thallium or lead, when the dehydrogenation metal is a Group VIII metal.Type: GrantFiled: December 10, 1990Date of Patent: April 7, 1992Assignee: Mobil Oil Corp.Inventor: Ralph M. Dessau
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Patent number: 5101077Abstract: A process is provided for the preparation of unsaturated carbonyl compounds having at least one cycloalkenic moiety in the molecule, which comprises contacting an allylic type unsaturated alcohol and a conjugated diene in the presence of a catalyst system obtainable by combining a Group VIII metal compound and a ligand containing one or more donor atoms selected from Group V A and VI A elements.Type: GrantFiled: March 13, 1991Date of Patent: March 31, 1992Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5087760Abstract: A process for the production of 1,3-cyclopentanedione, which is a versatile intermediate product for numerous active ingredient syntheses. For this purpose, a malonic acid ester is reacted with a haloalkoxybutenoic acid ester, the resultant bis-(alkoxycarbonyl) alkoxypentenoic acid ester is cyclized to alkoxycarbonyl alkoxycyclopentenone, the ester function is saponified, and finally the intermediate is decarboxylated to the end product.Type: GrantFiled: January 3, 1990Date of Patent: February 11, 1992Assignee: Lonza Ltd.Inventors: Rudolf Fuchs, John McGarrity
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Patent number: 5041678Abstract: Optically active isomers of alpha-damascone of formula ##STR1## wherein the wavy line designates a C--C bound of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula ##STR2## where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula ##STR3## where the asterisk identifies a center of chirality;index n stands for zero or 1;each of symbols R.sup.0 and R.sup.1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above;each of symbols R.sup.2 and R.sup.Type: GrantFiled: September 28, 1990Date of Patent: August 20, 1991Assignee: Firmenich S.A.Inventors: Charles Fehr, Jose Galindo
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Patent number: 4929762Abstract: A phenol and/or a cyclohexanone is prepared by dehydrogenation of cyclohexenone and/or a cyclohexenol in liquid phase under the presence of a solid catalyst comprising a platinum-group metal loaded on a carrier. The solid catalyst comprises a carrier selected from activated carbon and hydrotalcites.Type: GrantFiled: March 2, 1989Date of Patent: May 29, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Hiroshi Fukuhara
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Patent number: 4918239Abstract: This invention provides a method for producing cyclohexanone from cyclohexanol using oxidative dehydrogenation. More particularly, this invention comprises adding a certain amount of a gaseous oxidant to the cyclohexanol feed stream; and, converting the cyclohexanol to cyclohexanone over a CuO-ZnO catalyst.Type: GrantFiled: December 27, 1988Date of Patent: April 17, 1990Assignee: National Science CouncilInventors: Ikai Wang, Yu-Ming Lin
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Patent number: 4898988Abstract: A process for the preparation of .beta.-hydroxyketones comprising the catalytic hydrogenolysis of an aqueous solution of isoxazolines having the formula ##STR1## in a fixed bed reactor containing a transition metal catalyst at a temperature between 20.degree. to 150.degree. C. and a pressure from about 0 to 150 psig; wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, alkyl, cycloalkyl or aromatic group and wherein the aqueous solution of isoxazolines is substantially free of acids or buffers.Type: GrantFiled: March 13, 1989Date of Patent: February 6, 1990Assignee: W. R. Grace & Co.-Conn.Inventors: You-Jyh Lin, Harold Kloczewski
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Patent number: 4868337Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.Type: GrantFiled: December 17, 1987Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4846945Abstract: Oxidation of alcohols to ketones using bromine suffers from a side reaction of comparable speed in which a bromide substituted product is formed. Additionally, the use of bromine as reagent is relatively unpleasant and it creates a major waste disposal problem.The latter problem can be solved by generating bromine in situ by reaction between hydrogen peroxide and bromide ions or hydrogen bromide, but this inevitably increases the exposure of the alcohol to HBr/Br.sup.-. The selectivity of the process towards non-substituted oxidation depending upon the inherent deactivation or reactivity of the alcohol can be improved by irradiating the reactants with light of suitable frequency to generate bromine radicals in the mixture, and/or by controlling the rate of introduction of the hydrogen peroxide and controlling the extent to which mole ratio of HBr:alcohol is substoichiometric.Type: GrantFiled: September 2, 1987Date of Patent: July 11, 1989Assignee: Interox Chemicals LimitedInventors: Philip J. Turner, Vincent I. Routledge, Martin Jeff
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Patent number: 4701540Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.Type: GrantFiled: March 12, 1984Date of Patent: October 20, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4670605Abstract: A catalyst and a process to convert commercial cyclohexanol feed to cyclohexanone at a relatively low temperature at stable conversion levels for long periods of operation. This process and catalyst allow operation in the presence of water and high boiling side products. The process features high conversion efficiency and low by-product formation, by use of an improved CuO-ZnO catalyst promoted with an alkali-metal compound such as sodium carbonate. The catalyst is stable in the presence of water and heavy end products in the feedstock (up to 13%). The presence of water rejuvenates the catalyst, increases the conversion and decreases the phenol content in the product mixture.Type: GrantFiled: May 31, 1985Date of Patent: June 2, 1987Assignee: Industrial Technology Research InstituteInventors: Horn-Ming Chiu, Min-Hon Rei
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Patent number: 4628120Abstract: A preparing method of optically active ketones given by a general formula ##STR1## (wherein R represents a hydrocarbon group having 2 to 20 carbon atoms and R' represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups of R and R' may contain functional groups having no influence on the reaction. But, * represents an asymmetric carbon atom, and R represents a more electron donating group than R' (except when R=R') through the rearrangement reaction by using organoaluminum compound.Type: GrantFiled: October 16, 1984Date of Patent: December 9, 1986Assignee: Toyo Stauffer Chemical Co., Ltd.Inventors: Genichi Tsuchihashi, Keisuke Suzuki
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Patent number: 4618724Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.Type: GrantFiled: February 11, 1985Date of Patent: October 21, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hitosi Nozaki, Koichiro Oshima
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Patent number: 4616095Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4615830Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4613706Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: September 23, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4560804Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4560805Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4556742Abstract: .alpha.,.delta.-Diethylenic carbonyl compounds of the formula ##STR1## are made by an oxy-Cope rearrangement of an acetylenic alcohol of the formula ##STR2## in the presence of a catalyst based on a metal of Group Ib of the periodic table or palladium. In the formulae (I) and (II), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, each denote a hydrogen atom or a hydrocarbon radical R.sub.2 and R.sub.3 being capable together of forming an alkylene radical (--CH.sub.2 --).sub.n in which one or more carbon atoms may be substituted by one or more alkyl radicals containing 1 to 4 carbon atoms, n is 3 to 20 inclusively and R.sub.5 denotes a hydrogen atom.Type: GrantFiled: May 25, 1984Date of Patent: December 3, 1985Assignee: Rhone-Poulenc SanteInventors: Norbert Bluthe, Armand S. Falou, Jacques Gore
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Preparation of compounds of the 4-oxodamascone series, and novel scents from this class of compounds
Patent number: 4550211Abstract: Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably 40.degree. to 70.degree. C.,B. the resulting ketone of the formula IIIb ##STR3## is oxidized in a conventional manner, and C. if desired, the resulting compound Ib is isomerized in a conventional manner.Compounds of the formula A ##STR4## where R is one of the following radicals: --CH(OH)--CH.sub.2 --CH.dbd.CH.sub.2 (IIIb), --CH(OH)--CH.sub.3 (IIIc), --CH.sub.2 OH (IIId), --CH(OH)--CH.dbd.CH.sub.2 (IIIe), --CH(OCOCH.sub.3)--CH.sub.3 (IIIf), --CH.sub.2 --OCOCH.sub.3 (IIIg), --CO--CH.sub.2 --CH.dbd.CH.sub.2 (Ib), --CO--CH.sub.3 (Ic) and --CO--CH.dbd.CH.sub.2 (Ie).The compounds IIIb to IIIg, Ib, Ic and Ie are useful scents and aromas, and furthermore may become important intermediates for novel carotenoids.Type: GrantFiled: March 12, 1984Date of Patent: October 29, 1985Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann -
Patent number: 4532347Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.Type: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan